You’re Following the Crowd Without Realizing It— Toni Will | Ep 225

On this episode of Relatable Wisdom, I had the pleasure of sitting down with Toni Will, a trailblazer who lives by Mark Twain’s mantra: “Whenever you find yourself on the side of the majority, it is time to pause and reflect.” Toni’s journey—from the banking world to becoming the general manager and only female governor of a men’s professional hockey team—is full of bold, rebellious decisions and powerful self-reflection. We talk about what it feels like to be the only woman in high-pressure rooms, how choosing sobriety (not because of crisis, but for clarity and more intentional success) changed her life, and the importance of “coloring outside the lines.” Toni’s insights will help you question default thinking, redefine success on your terms, and trust your ability to weather tough moments. If you’ve ever wondered how to make unconventional choices or stick to your values even when it’s uncomfortable, this conversation will give you both inspiration and practical strategies. Plus, learn how Toni’s upcoming book, Rebellious Success, and her leadership philosophy can fuel your own growth and gutsy decisions.

Connect With Toni Will
Website: https://toniwill.com
Women In Podcast: https://toniwill.com/women-in-podcast

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Chapters
00:00 Introduction And Welcome
01:20 Toni’s Life-Changing Quote
02:24 Choosing Sobriety And Standing Apart
03:47 Breaking Barriers In Hockey Leadership
05:28 Navigating Microaggressions And Speaking Up
06:49 Building Confidence And Overcoming Internal Barriers
08:45 Leading Authentically And Her Leadership Pillars
10:08 Embracing Career Detours
12:37 Recognizing Opportunities And Following Breadcrumbs
13:58 Facing Fear And The Power Of Challenge
16:22 The “More” Behind Going Alcohol-Free
17:58 Surprising Lessons From Sobriety
20:05 Defining Rebellious Success
21:42 How Her Definition Of Success Changed
23:51 The Value Of Failure And Trying
25:12 Fill-In-The-Blank Wisdom Game
27:18 Healthy Rebellion Versus Contrarian Sabotage
28:34 Pausing Before Responding
29:57 Where To Find Toni Online
30:22 Closing Reflections And Farewell